I rewatched Life's Still Unfair for the 4th time today (this time with my Dad - who loved it), so here: finally have my additional mitm headcanons post-LSU.
(for my original post-mitm headcanons, see here. Everything that realistically can fit in the gap between the shows is still canon to me)
Stevie and Cynthia are Leah's godparents. They were the only people in Leah's life who knew the truth, and regularly told Malcolm he was crazy for his choices. Malcolm is also Max's godfather because him and Stevie are just bonded like that 5eva
Dewey tried to live by his word and be much kinder to Jamie and Kelly than the older boys were to him, but did also follow through on throwing Jamie under the bus when he needed an out (first time he did it was when Lois caught him with a girl in his room)
All the nicknames the boys had for Kelly growing up just happened to be gender-neutral (Kid, Squirt, Buds) which always made them feel comfortable
Kelly also was the first of the Wilkerson kids to love wearing hand-me-downs
Jamie was on the swim team at school, and worked part-time as a lifeguard at the local pool as a teen. He also played the drums in a band
My previous chef headcanons for Reese still stand, but when he was about to hit 30, he basically panicked about everything being too good to be true and quit his job/blew up his life which led to him getting dumped by his long-term boyfriend (maybe fiancé)
In his 30s, Reese then just did a bunch of random jobs here and there, but never long enough to self-sabotage. During lockdown he dabbled with OnlyFans too (Lois shut that down fast). He also got married again, thinking the Francis x Piama approach might work for him... it didn't.
Dewey's music is mostly art for arts sake, but occasionally he dabbles in scoring for films/tv. Part of the funds of everything he does goes towards supporting special needs education, and also access to the arts for working class kids
The siblings (esp Dewey and Reese) relish in being uncles, and try and make up for the lost time with Leah. For Reese, this looks like helping her ace home ec, maybe by sabotaging her peers, and for Dewey it looks like giving her free concert tickets when he's in town
Tristan connects with the fam immediately, and while Piama wants to resent her for how much easier it was for her, she's just so darn likeable
Leah calls her grandparents to talk to them every day - it's one of Hal & Lois' fave parts of the day (and while he won't admit it, Malcolm kinda loves it too)
Leah also has a group chat with Hubert and Kelly, which is as odd as it sounds
Dewey 100% knew about Professor Dumb-Dumb, but asked for a cut of the income in exchange for silence, and that was just agreed. Jamie also knew but just enjoyed the content and never thought to tell
Lois was true to her word and did get excited about Francis & Piama's baby once she'd shifted some other things off the list, and when she went into labour, Piama found herself asking for Lois there with her